


My Brother Saves Me From Selling My Virginity… But Somehow I End Up Losing It Anyway

by HomerSoc



Category: Original Work
Genre: Brother/Sister Incest, F/M, HomerSoc, Impregnation, Loss of Virginity, Prostitution, Stripping, gwa, script offer
Language: English
Status: Completed
Published: 2021-01-18
Updated: 2021-01-18
Packaged: 2021-03-17 02:33:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,165
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28841688
Author URL: https://archiveofourown.org/users/HomerSoc/pseuds/HomerSoc
Summary: She was going to sell her virginity to some random guy because she was desperate for money. She even had her brother drive her to the hotel, telling him it was for her to meet her friends. But she couldn't do it. But when her brother offered to give her the money she needed, with no strings attached... well, that's when she decided she could.
Comments: 1
Kudos: 19





	My Brother Saves Me From Selling My Virginity… But Somehow I End Up Losing It Anyway

I’m sorry about tonight. You’re way too kind to you little sister. First I ask you to drive me somewhere to meet my friends at a hotel. But then when we get there, I tell you to bring me back home. You must be really confused.

Now that we’re safely back home, I’m going to come clean with you. It wasn’t to meet some friends. It was for… for a date. But, one of those dates where you get paid for it. For the company, and… and the sex. 

I’m not an escort though. I mean, I was going to be, but I couldn’t go through with it when we actually pulled up at the hotel. I’ve never even had sex. Which is why they were willing to pay extra. A friend of a friend arranged it. And they’ll be mad now, and I won’t have the money I need for… well, stuff I need. 

I even lost money on this entire thing. They wanted a school girl outfit, and… well, if I take off this stupid coat, that’s what I have on. It wasn’t cheap, either. I mean, it is nice. It’s somewhere between an actual school girl and a stripper in style. Maybe music video schoolgirl or something?

You aren’t mad, are you? Or disappointed in me? I mean, I didn’t go through with it obviously. But I was planning on it until I chickened out. Now that I’m home, and realizing that I won’t have the money I was counting on now, I’m second-guessing my second-guessing things earlier. It’s not too far, and I’m not that late yet. I could ask you to drive me back again, except now you’d know what it was for. Maybe you’d refuse, although you’re so nice you might do it anyway if I begged you. But then I’d have to face you after the cab dropped me off in the morning.

[pause for reply]

No, I’m too embarrassed to say how much money I need, or what price I was putting on my body and my virginity. I can’t say.

[pause for reply]

How much? No, not that much. I wish I could make that much from this.

Is… is that how much you think I’d actually be worth though? It’s weird, but it’s kind of flattering. Even coming from my brother. 

Never mind that though. I screwed up. Really, I screwed up a lot of things recently, but I really screwed up by not getting out at the hotel. I need to go back. I’d call a cab, but I literally have no money to pay them with. I… I hate to do it, but can you drive me again? Or at least loan me cab money?

[pause for reply]

You’ll give me the money? That would probably work out better. It would be an awkward drive back to the hotel now for us, and-

[pause for reply]

Wait, you’ll give me the money I need? Actually, the money you said you thought I was worth? You… you actually have that kind of money?

What am I saying? Of course you do. You’re the responsible one. You have college and the job on the side, and financial aid, and probably money you’ve been saving all of your life. I don’t want to take it. But I can’t really say no.

Um, just to clarify though. Is this a gift to your little sister… or were you thinking more payment for… well, you know. What I was planning on selling tonight anyway.

[pause]

Oh God. I’m so sorry. I’ve just made tonight infinitely weirder, haven’t I? It’s just that… I don’t know. I guess the entire selling my virginity thing was on my mind, and I suddenly wasn’t certain on what you were proposing here. But I should have been, of course. You wouldn’t turn your sister into a hooker by paying her for sex. It’s just that when I took off my coat, you seemed to find my schoolgirl outfit kind of interesting. I guess any guy would though.

I wouldn’t have actually done it anyway. I couldn’t, of course. You’re my brother. I would have had to get to the hotel somehow, or find a plan C in all of this.

Well, now that we’ve got a happy ending to all of this, I guess I should go to my room and get out of this outfit and wash off all of this makeup. Then maybe do some homework for Monday because finals are coming up. Even though I’m not in college until next year doesn’t mean I don’t have to study as hard as you.

So I’ll just go now, and, um…

Look, I’m just going to put this out there. You seemed to like this outfit, like I said earlier. You’ve been really nice to me. Not just today, but especially today. 

Would you maybe like to watch me take it off?

Not for money. The money thing is entirely separate from this. That was you being nice to me. Me doing a little striptease for you would just me being nice back.

It’s okay to say no of course. But… it’s okay to say yes. I won’t judge. You didn’t judge me when I said I was going to sell myself for money tonight. Now that you’ve seen me in this outfit, it’s only natural that you’d want to see what’s under this blouse, or what’s under this skirt. It’s not like we’d be doing anything really wrong. It would be like if you walked in on me in the shower, or changing my clothes in my room, except not really like that. You know what I mean though.

Honestly, if you say yes, then I’ll feel like I’m at least paying you back a little for what you did for me. So… it’s so very okay to say yes.

Or really, if that’s too hard… just nod your head.

[short pause] 

You nodded. I didn’t think you were going to. I think it was only because I made it so you didn’t have to say anything. But it’s totally okay. Look, um… sit down on the couch, and that will give me plenty of room here.

There. Wow, we’re going to do this, aren’t we? I’m going to strip for my brother. But don’t worry. Like I said, I’m okay with it.

Let me just dance a little for you. I don’t know if you’re the type to go to strip clubs, but I’ll try to give you that experience. Well, minus the cover charge and overpriced drinks. I’ll sway back and forth, and slowly start undoing the buttons on this blouse. There were already a few undone as it was, so it doesn’t take long. You can see my bra now, which isn’t really schoolgirl appropriate, and you can see more as I pull the blouse off entirely. Now it’s just the bra, the skirt, and the stockings.

I’ll take off the skirt now. If this gets too weird, tell me and I can stop. But make sure you’re stopping it for you, and not for me. I want to do this, and I want you to like it. 

I take off the skirt, and there’s panties to match the bra. This is more of me than any man has seen before. But it’s okay, because you’re my brother. That’s why I can start undoing the bra, before carefully taking it off.

Do you like them? Do you like my breasts? I thought I was going to be showing them to some stranger tonight. Doing far more than that, really. It’s actually a relief to be showing them to someone like you instead.

You do like them. I can tell from how you look at them. That gives me courage to keep going, and to slowly take off the panties. Somehow I can do that more confidently in front of you than I could in front of some strange man.

I… I shaved myself there, as you can see. It was a special request by my client. It actually feels kind of good to have it so smooth like this. 

I could take off the stockings, too. I probably should have done that sooner. I really kind of like them though, and was going to wear them for a while. I think you kind of like how they look on me though.

Well, I guess we’re done now. I can gather up this outfit from the floor now and go to my room, and you can go to your room, and… well, I can guess what you’re going to do after this little show.

[sigh] There I go again. I keep making things weird. Yeah, we both know you’re going to go back to your room and masturbate over me, but I didn’t have to say it. It’s okay. It’s natural that you would want to. Don’t feel bad about it at all.

Except now that I’ve said not to, you will. You won’t do it. Maybe you’ll take a cold shower, which may or may not help. Either way, you’ll probably go to bed frustrated. Which may even lead to you having a wet dream about me.

Damn it. I should just shut up now, shouldn’t I? I should take my things and go, and let you go, and not make things any weirder.

Or… I guess I could masturbate you myself. 

You need some release after all of this, and now I’ve made it so you won’t do it for yourself. So I need to. I know I can talk you into it. When you leave and go back to your room, you’ll just have the memory of me to keep you excited, but without my direct presence, you won’t jerk yourself off. But with me in front of you, and taking a few steps closer slowly, you can’t find it in you to tell me to stop, can you?

It’s okay. I’ll just kneel in front of you and unzip your pants. I can tell before I even do that what I’ve done to you. As I pull your pants down I can see how your cock swells in your boxers. All because of me. So I’ll take the boxers off too.

I… I’m going to touch it now, okay? It will be weird, but it will be good too. And it won’t be anything we need to be ashamed about. It’s just a handjob, and it’s just because you’re so hard right now, and it’s all because of your little sister.

[laugh] It jumps a little as I wrap my hand around it. You jumped a little. And I did too, I guess. My hand barely fits around it, but I start to move it up and down slowly. 

You like that, don’t you? It’s okay. Don’t feel guilty about it. Just feel good, and I’ll just keep moving my hand up and down, and twisting it a little sometime. I could go up and get some baby oil from my room, because that would really help. Or… would you mind if I drooled a little spit on it? Just to lubricate things a little.

Okay, one sec. I’ll kind of lean in some more. I probably smell real nice, what with the shower and shampoo earlier, and then the perfume. Just focus on how nice your little sister smells as I let some saliva trickle down onto my hand and your cock.

There. Yeah, that’s so much better. My hand moves so much easier, and… [laugh] well, you should see the look on your face. Now I can give you a proper handjob. There’s a box of tissues next to you for when you cum. 

Unless… you’d like to cum on me instead?

Nowhere near my pussy. But maybe on my breasts? Or my face. I was going to spend some time washing it to get this makeup off anyway. But not in my mouth. I’ll keep that tightly shut. That would be kind of like if I sucked your cock and you came in my mouth.

Oh God. Your cock just jumped.

It was when I talked about your cumming in my mouth after I had sucked you.

It did it again!

You kind of want that to happen, don’t you?

Correction. You really want that to happen.

It’s okay. Please don’t be embarrassed. It’s only natural that the idea would excite you, even with my being your sister. My hand is pretty good, but with my lipstick my mouth must be looking pretty nice. Especially these lips..

In fact, I’ll show you how okay it is.

[begin blow job noises]

No, it’s okay. I probably would have had to do this for that stranger tonight, and then a lot more. The least I can do is suck your cock and let you cum in my mouth. Maybe even swallow it. But not because you paid me. Because I want to. For you.

I would have done this so reluctantly for him. I probably would have gagged and been clearly uncomfortable with it, even if I tried to put on a good show. But doing this for someone I care for, and love… it’s different. Even if you’re my brother. 

Would it be weird if I played with myself as I do this? It’s just that I feel so smooth, and it feels so good, and I’m a little turned on. And I’m doing it already, so I’m more begging for forgiveness than asking for permission. At this point, I’d be the one going back to my room and masturbating if I didn’t get some release here as I suck your cock. We’re still not doing anything all that bad. At least not on a scale of one to fucking some stranger for money, or fucking my brother for any reason at all. Definitely for money but for any reason really.

Wait. Do you want to touch it? Not your cock. I mean my pussy. It’s so nice and smooth. I couldn’t suck your cock at the same time, but you kind of got a head start on me. You could touch me for a bit, and then we could kind of get me caught up to you, and go back to this, and then cum together. But entirely apart, in that most important way.

[stop blowjob noises]

I’ll get off of the floor and sit on the couch next to you, my stockinged legs spread apart. I’ll take your hand because I don’t know if you’ll dare do it yourself, and put it between my legs. I can show you what to do to me. Touch me there, and there… I’m sorry I’m so wet, but also not sorry at all. Just don’t put your fingers inside of me. 

[moan] Oh God. You’re the first man to ever touch me there. Not the first girl, and I’m not just counting myself, but that’s a long and sexy story that I might just tell you sometime. But the short version is I was sleeping over at my friend's house. Yes, you know the one. It started as practicing kissing… you know, for boys. Then somehow it turned into practicing rubbing pussies, you know, for girls, even though that wasn’t part of the original plan. It would have turned into licking pussies if we didn’t hear her mother walking down the hallway to ask us if we wanted brownies. So I never got a chance to have my pussy eaten.

Unless… you want to now?

I’d let you. It’s still not anything too bad. I sucked your cock, so eating my pussy can’t be any worse on the morality scale. I can tell you want to, and I kind of want to try to right now, too. I’m so bold right now, which isn’t really me, so I have to run with it. Now that you’ve taken care of my financial problem, I don’t need to do anything sexy until I’m ready for it, and that could be a while. So I should get it out of my system tonight.

I’ll turn now and lie down on the couch, my legs still spread, and my wet pussy exposed to you. I’d feel so vulnerable right now, with a man and his hard, naked cock so close to me. But you’re my brother, so I don’t need to worry. I just lie here as you lean down and put your head between my legs and- [moan]

Oh fuck. That feels good. Better than fingers… much better. It feels naughty too, because you’re my brother. But somehow that adds to how good it feels. I wasn’t expecting to feel any pleasure tonight with what I had planned, but you’re making me feel so much. 

I grab onto your head, desperately trying to hold your mouth against me, afraid that you’ll take it away and deny me this pleasure… the feel of your tongue and lips doing things to me I never dreamed of. I moan and squirm on the couch as you drive me absolutely wild. I think I’ve caught up with you now, but please don’t stop. Make me cum from this. I can cum so many times in a night when I’m playing with myself, so I’ll be good for when we go back to me sucking your cock. But I need this orgasm so bad right now. I deserve it, and you deserve to give your sister her first orgasm from a man’s mouth.

[improv to orgasm]

Oh God. That was incredible.Thank you. And, um, sorry about your face. I got really wet there towards the end. I can clean it up before we continue. I can just grab some tissues here.

Or… I could lick your face clean.

I’m sorry. I keep making it weird, as if it could get weirder. But I kind of want to taste me, and I’m right there all over your face. At least the mouth. You don’t mind if I pull you up from between my legs so I can do that, do you? I can trust you not to try to do anything with your cock, even though that will put it dangerously in the proximity of my pussy. Of course I can.

Then I can start licking your face, but only to clean it off and to taste myself on you. Licking your chin, and then your cheeks… and then your lips.

[kiss]

Hey, you weren’t supposed to open your mouth there. But I’m not too mad.

So, um… we’re going to fuck, aren’t we?

We shouldn’t. We shouldn’t have done any of this. Maybe the strip tease, but everything after that was straight-up a bad idea. Not anything I regret right now, but that I probably will later. Just like I will regret us having sex.

But it’s still going to happen. We’ve come too far not to cross that laat barrier. Even though it shouldn’t happen. It can’t happen. I’m your sister. And I’m not on birth control. They were going to have condoms in the hotel room, because I wasn’t trusting a stranger, no matter how much they paid. But I don’t have any of my own, and if you do, let’s not talk about it. 

I can tell you’re torn. You want to be the good big brother. You want to protect your little sister and her virginity. 

But you also want to fuck my brains out right now.

Do it. You earned the right. Not through money. But by being nice, and being a good big brother, and also by giving me such an incredible orgasm. We’ll never be in this position again. I mean literally, you’ll never be lying on top of me naked. But we’ll also never be this close to sex. At least I don’t expect we will be, because once we’ve cooled down, there might be some regrets. So why not really give us something to regret later? Especially because I think it will feel so good now?

That’s it. I can feel your cock pressed against me. I’ve felt it in my hand, and in my mouth. I so desperately didn’t want to feel a cock inside me today until suddenly I did. Even if it’s my brother’s. Even if it’s dangerous, because I could get pregnant. But I honestly don’t care too much about either right now. Even as you press harder against me, I don’t feel panic. Just lust. And as it slowly starts to slide in, I’m not scared or turned off by what we’re about to do, or who is about to do it to me. Not even as you…

[moan as entered]

As you take me, completely. Your cock is buried inside me now. What I was going to sell for so much I happily give to you. Just keep it right there for now. And look at me. Look me in the eyes. This is your sister you’re fucking. Never forget that, because I never will. Maybe I’ll have trouble meeting your gaze later when we meet in the hallway or eat meals together. But for right now, I can’t get enough of my brother’s face right above mine, and seeing the pleasure my pussy is putting there.

Now move. I’m more used to you, and we both need to feel it. I’m so wet and so turned on still, even with this being my first time. Despite that, you move easily in me, and it sends little waves of pleasure in me each time you move back into me. This is even better than your tongue, and from your face I can tell this is better than my mouth was for you. I’ve never seen such lustful expressions on your face before, but I love them. And I love them all the more for knowing I’m putting them there.

You can go harder. I’m more than ready for that. I’m sure my client wouldn’t have been as gentle as you are, and I wouldn’t have been as wet. I definitely wouldn’t be feeling so much pleasure, and feeling another orgasm building inside of me. 

I shouldn’t be. This is so wrong, and so horribly messed up. But so right as well. I’m fucking my brother. And you’re going to cum in me… maybe even impregnate me. It’s so wrong, and stupid, but all I can think of is how I would look pregnant with your baby. It would make things so much worse between us, especially as I showed more and more and couldn’t hide it from mom and dad. At least when the baby comes, if it looks like you they’ll just blame it on genetics. 

[moan] I’m turning myself on with that kind of talk. Despite being a virgin until a few minutes ago, I have a wild side I never knew about. But it turns you on when I talk like that too, so maybe it’s a family trait. Then it’s not our fault at all, and we can’t be blamed for it. This is all mom and dad’s fault.

We’re getting close now. Don’t you dare think about pulling out. I will never forgive you if you do, although I can’t promise I’ll forgive you or me for any of this later. But I need you to cum in me… maybe even impregnate me. [moan] Oh yes… impregnate me with your baby, big brother…

[improv to orgasm]

[pause]

Well, um… that was… something. 

I guess maybe you should pull out and get off of me now.

Definitely feeling a little awkward now, with the sweat of our bodies covering us, and my brother’s sperm a very physical presence in my womb.

This is where I gather my clothes, and go to my room. And you gather yours, and go to your room. Maybe we both want to shower but neither one wants to risk seeing the other in the hall, so we’re just left in our rooms with the memory of what we just did. Then we’re distant over breakfast tomorrow morning, and mom and dad think we had a fight, when just the opposite is true. And we wait to see if I get pregnant. But you still finish college, and I still go, even if I may need to take some time off for a baby. There will always be this night forever trapped between us.

So that’s how it ends, I guess. Or how it starts.

Or… and I’m just putting this out there… you carry me to your room or mine, and we hold each other and fuck our way through this until we’ve made peace with it, and face a future together that won’t be easy, but will at least have each other and lots of sex, and probably babies.

So… what are you going to choose?


End file.
